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Islamorada Overseas Highway

Islamorada, FL, USA

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Opening Snapshot

There are vacation homes, there are estates, and then there are houses that make you wonder what it would feel like to live like a billionaire for a month. Islamorada Overseas Highway is that house. You arrive in Islamorada, pull through the gates, and almost immediately the place starts showing off. Crystal sinks in the bathrooms. A grand staircase. Chandeliers. Over-the-top bunk rooms that look like they were designed for the children of rock stars. An indoor basketball and pickleball court. A private beach. A 100-foot dock. A rooftop terrace. A pool and spa. And when the sun goes down, you can watch a movie outside on a 300-inch screen. Nothing about this house is restrained, and that is exactly why it works. This is the Florida Keys fantasy turned all the way up: wake up on the Atlantic, take the boat out, come back for a swim, play basketball indoors, have dinner overlooking the water, and end the night watching a movie under the stars. For a little while, this is what your life looks like.

GUESTS

BEDROOMS

BATHROOMS

PETS ALLOWED

POOL

HOT TUB

FIRE FEATURE

DEDICATED WORKING SPACE

WINERY ESTATE

EV CHARGING

HOME FOR SALE

Virtual Tour

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What we love

This house understands the assignment: make every day feel ridiculous in the best possible way. The Chateau is packed with moments that make you stop and say, “Wait...this is in the house?” The bathrooms alone have details like crystal sinks that feel more penthouse than beach house. The bunk rooms are some of the most elaborate we have ever seen, turning what is usually the least glamorous sleeping arrangement into something kids — and probably plenty of adults — will fight over. Then there are the toys. Indoor basketball and pickleball mean nobody cares if it is raining or 95 degrees outside. The fitness setup is serious. The pool and spa feel like their own private resort. Rooftop and oceanfront terraces give you multiple places to disappear with a drink. And the 300-inch outdoor screen turns movie night into something closer to a private premiere. But the Atlantic is still the star. You have your own beach and a 100-foot dock right outside, so the Keys are not something you drive around trying to experience. They start in your backyard.

Keep in mind

Subtlety is not part of the program here. This is grand, ornate, highly designed and unapologetically extravagant. If you want a barefoot little Keys cottage with weathered wood and a hammock, this is not that house. Islamorada Overseas Highway is for someone who wants to arrive and think, “You have got to be kidding me.” Islamorada is also more drive-to-dinner than walk-to-town, but at a property like this, leaving the house can start to feel optional.

Work Mode

There is no formal office, but finding a quiet place to work in a house this large is not going to be a problem. For an executive retreat, it may be even better: finish the call and you can be on the dock, in the gym or on the basketball court a few minutes later.

The brag

Joe B. lens:
I do not think we have another house on The Joes that even belongs in the same category as this one. Crystal sinks, dramatic staircases, chandeliers, crazy bunk rooms — every time you turn a corner there is another detail that feels completely over the top. I love that it commits to the fantasy.
Joe R. lens:
This place is insane. Indoor basketball and pickleball, a serious gym, a huge outdoor movie screen, a private beach and your own dock? If I were imagining how a billionaire music mogul might build a Florida Keys vacation house, this is pretty much it.
Together we agree:
You do not book Islamorada Overseas Highway because you simply need seven bedrooms in the Keys. You book it because for one month you want to know what it feels like to live an absolutely ridiculous life.

Getting around

Islamorada is one of the great boating and fishing destinations in the Florida Keys, with reefs, snorkeling, diving, fishing charters, marinas and waterfront restaurants all nearby. Morada Way, Founders Park and the History of Diving Museum give you reasons to explore on land, while Miami is roughly a 90-minute drive in favorable traffic. But this is one of those rare houses where staying home may be the best plan of the day.

Joe-Tested,
Joe-Approved

It is not one feature. It is the moment — probably sometime during the first hour — when someone in the group says, “Oh my God. Are we actually living here?” That is Islamorada Overseas Highway.

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Additional Property Details

City & State:

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From the Owner:

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Amenities

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